Paragliding the Matterhorn - a Startup Allegory

Continuing my week through Italy for ATP Finals, I started in Venice and worked west. At the ATP NextGen in Milan, it showcased the top young stars (aged 21 and younger). Happily, it concluded with our hometown hero and San Diego Open champion's victory - Brandon Nakashima.

Waiting to go to Turin (or Torino), I had a couple of days before needing to arrive for the ATP Finals.

Paragliding and the Matterhorn. Soaring through Zermatt for the first time. 

Startup's Journey

"No matter what you do, building a start-up will be a very challenging journey…if you don’t start with enough passion, you won’t get to the other side. If you don’t fall in love with the problem, you simply will not be able to get through the journey.” 
- Uri Levine (Co-Founder of Waze) "Fall in Love with the Problem" (releases 1/17)

Trying to decide where to go next, I scanned the map and then the weather forecast. November is known for rain and cold weather in that region's shoulder season. Not yet cold enough for snow, yet too cool for most fairweather tourists. Near the Italian/Swiss border was a lifetime bucket list. Marked with a heart on my Google Maps was a mountain called the Matterhorn.

Clear weather to see the mountains

The key luck factor was the weather forecast. It was nothing short of a miracle in November to get clear skies and 50s a high temperature! With just a 48-hour window, it was time to go. Let's do this!

Eagle's Nest

I booked a small AirBnB suite that only crazy backpackers or last-minute cowboys like me even consider. With this once-in-a-lifetime chance, the detour is the adventure. The Obstacle is the Way.

Instead of going South back to Milan, I would detour North to Switzerland. A taxi took me from my Italian castle to the Stresa main train station. This would be the first leg of many to reach Zermatt (basecamp for the Matterhorn). Several trains, buses, shuttles, and lifts later - I would reach the snow.

Lost in Translation

Nobody was working at 6:30 AM, so I only had the option of using the automated Italian train ticket system. I entered my destination, "ZERMATT," and the error screen flashed back several times. "No route found." Uh oh.

I pulled up Google Maps again and saw I'd have to make a few transfers. Reaching Zermatt would take a few different modes of transportation (Italian Train, Swiss Train, Bus, then shuttle).

I ate a quick cafe breakfast and waited outside for the train, faced with 2 platforms - A and B.

Again, there's still no staff at the station. Nobody is working at the window counter. So I ask one lady waiting that looks like she's a local. Was this the platform for the train to Brig?

Brig? No, I think you need to take the other platform.

Unfortunately, the "other platform" was for regional trains. The 30 Euro ride I was supposed to take was an express one to connect directly, but because of rail delays, it was actually 15 mins behind.

When I crossed over, I checked the train schedule signpost, and Riga was listed with the departure time being +/- 3 minutes from the ticket.

I hopped on, but immediately I should have noticed something was off...Getting on, the creeky rail car doors were so old, it barely even slid open as one rider was getting off. It was nearly empty inside, with dusty windows and all adjacent cars empty. I quickly realized that this regional train would have 8 stops and take 30 minutes longer.

Accepting my fate, I enjoyed all the little towns along the way. Minutes later, I finally saw my express train whisk by. An elderly gentleman on board kindly explained that I would have to rebook when I arrived at the town of Domodossola. After showing him the translation, he verified my best hope was at the main station.

Switzerland's Ski Resort towns

After my transfer from Brig to Riga, I noticed a big contrast between the surroundings and passengers. This was ski country and early season, so many were going there for a weekend getaway. The Swiss trains were noticeably cleaner, quieter, and better staffed.

On the train, I received an Airbnb text from my host after I told him I'd be behind an hour due to the transfer. He texted back, "no problem - hey, do you want to go paragliding?"

He knew a local guide who could often take his guests up if the weather was clear and the winds were favorable. Apparently, fate wanted me to go fly that day.

Scaling the Matterhorn is a Startup's Journey

Anyone can pay for a postcard at the tourist shop. The rich come to the ski resort town of Zermatt and take a lift to the top. Reaching it on foot, as one of my Stanford mentors did as a youth, is another matter. Fundraising angel or seed capital takes enormous perseverance in facing repeated hurdles, uncertainty, and rejection.

With group vacation planning over the years, I've wasted so much time talking and trying to persuade others to bring them along. Most desire the glitter of glory but have no appetite for the grind.

IG travelers can live vicariously through other photos or videos. But to truly separate between the hype and the reality requires you to put boots on the ground with due diligence.

CES 2023 Eureka Park - Gallery of Flops - the Startup Graveyard

In the Cold Start Problem, Andrew describes the hundreds of thousands of startups in the US annually, How many actually can get the funding they need to launch? Even pooling the "easy fruit" among the 3 F's: Friends, Family, and Fools, relatively few make it out of the base camp.

How many strangers or VCs will take the plunge with them? Less than 10% can get sustainable funding. Much rarer to hit the critical 5x, 4x, 3x in the first 3 years of Unicorns.

Everyone will tell you that your idea sounds good when you're presenting. Nobody doubts your conviction. But when it comes to crunch time - how many would put down their own money to go on that one-way ticket with you?

Anchors are everywhere to ground you in life.
Always ready to tell you no or what you can't do.
What you need to find are the lightest feathers for Wings.
Build a solid team that acts as its critical bonding glue.

It takes weeks, months, and even in my case, years just to map out the route and get close to VC investing. The small fortune you need to spend just to arrive is an obstacle for most and a barrier to entry for all but accredited investors. Sifting the wheat from the chaff.

"The door is going to open for a slipt second. Whether you choose to jump through it or not, it's not going to be there very long." 
- James Cameron (MasterClass)

Often, the forecast is grey with a rainy mix in November. Before the trip, I saw the 14-day forecast had a 25% chance of making a launch window.

Eternal Optimism - the humbling task of fundraising

Still, as most athletes, we always train and prep everything to give the best chance to go. In tennis, you prep your footwork before the ball approaches - even if there's only a 5% chance it will land inside the court. You put in those long hours in the gym, long before spending those final few seconds contacting the ball.

I still bought my train ticket as far as Stresa and then took a day-to-day outlook to see if I could ascend or turn back. Since I had a chance, I decided not to waste time and booked the first train in the morning. These are the moments you cannot always plan for.

Travel teaches you how to rebound from setbacks.

Getting delayed an hour put my timeline completely off the rails. My connection west at Riga was now pushed to the right. I had to buy a new ticket on the Swiss train to continue forward.

Delays like catching the wrong trains can be out of your control.

Still, you should plan forward, because your premise and goal haven't changed despite that roadblock. It is all part of the adventure and even when things go off-script, it makes for great stories later.

Bruno and the Air Taxi

"I'm Bruno. Follow me - we don't have any time to waste if we are going to catch the next train up!" When I arrived at the meeting point, he informed me this would be a rush.

So immediately before he discussed the price or details, he had me wheel my luggage to his ski office about a half mile away. Luckily, he had an extra pair of snow boots and a parka he could lend me before we ascended.

Bruno imparted a strong sense of urgency and determination. Barely any time for cordial greetings or learning much more than my name or where I was from, we were off. I had some doubts. Did I have enough warm layers? What if my camera came flying out of my hands? Could we make the train?

To fly or to die; there is no try...

Ruminating about worst-case scenarios or past mistakes won't do you much good. Neither does panic.

Sometimes, you need a seasoned guide who will push you. Let go and jump.
You must have some faith you can get the funding you need once you've reached that bridge.

Unlike a steady W2 salary job where you work, earn, invest, and hopefully retire. In the paraglider's scenario, you pack all your gear and return to the Earth either smoothly or not smoothly.

Book that one-way, but don't plan on returning the same way you go up - "Burn the boats" analogy

Someone asked me why I attempted to paraglide on my first Matterhorn visit. Why not just enjoy the view from the top? Precisely because I knew I would not be here again, and I didn't want to regret that I didn't maximize my potential when I got there that day.

Para-waiting: the patience art of fishing

Taking small steps and being content with incremental progress is not the mindset of market scouting as a startup entrepreneur. In reality, it is about shooting for the moon or bust; going for the proverbial hockey stick curve.

We prepared the sails when we trekked another 20-30 minutes to the cliff's edge. Simply admiring the view would not allow us to catch that critical bit of wind to get off the mountain safely. The equipment rollout took another 10-15 minutes of detailed preparation.

Never step on my lines, I remember Bruno warned. He wasn't kidding.
It's just thin little colorful threads that keep a shallow foil of plastic up to defy gravity. Small threads are the only thing separating a smooth descent from a spiral of death.

I equate this nervous time of uncertain anticipation to the negotiation exit phase in startups.
It is a game of chicken with the wind and nature. Sometimes you prep everything perfectly and get all the details right, yet you don't get your shot. Sometimes it is the right idea, at the wrong time. All you can do is put it all out there and pray to the Wind Gods for the fateful breeze.

Be ready to cast into the falling tide

To quote Arthur Brook's book - Strength to Strength - you must be ready to "cast into the falling tide." During the receding waves, when everything is going out, that's when the fish are biting. As counter-intuitive as it may seem.

The only mistake you can make is "not having your line in the water."

In the heart of the pandemic or just before reaching the teeth of the Winter, many people get cold feet. TopCourt was a perfect example of a pandemic startup - scaling up when the world was shutting down.

It rode the e-learning wave when tennis was shut down. In 2020, when the fans couldn't go to the tennis players, we brought tennis players to the fans. Now broadening to pickleball and introducing fans to the game. VC money was backing IPOs such as Airbnb.

Embrace running against the wind

All of a sudden, I heard the command.
Start forward, ok now faster, faster!

I paced forward with the harness around my waist.
After 20 or 30 yards, I saw the edge round off and drop down.

Signing the purchase agreement to sell your company through acquisition had the same halting feeling of guilt. On the one hand, you have your baby. On the other hand, you have to let it graduate and grow.

It's like waiting for the postman to deliver your college acceptance letter. Waiting weeks or months. Sometimes you expect a possible counter. It feels like an eternity.

You may constantly wonder if you should have gone earlier or asked for less.

Maybe this is how Icarus felt?

I remounted all the gear and readjusted all the lines. Take two. He seemed confident we would try and succeed soon. The socks began to flutter, this time for a few seconds longer.

Again, I started moving forward. Faster now, he ordered. I moved faster, taking extra care not to clip my feet. We ran straight for the cusp of the hill.

The boots and a web of metal harnesses bounced up and down. I could feel a slight pull on my hips and shoulders. The cliff moved too far away from my feet to reach. That was my point of no return.

I felt my legs pull up. As calm and light as the sky now. It enveloped me now in its heavenly hug. Airborne.

Art of letting go, timing the jump, overcoming fear

Before getting on that train, make sure you've made peace with yourself. When you look down off that edge, it is best to ensure you don't have some hidden phobias or deep-seated regrets lingering. Anyone with great anxiety about heights (or fears of bankruptcy) should not launch.

At the moment of truth, your thoughts flash before your eyes. Don't have those regret in your heart. I lept (or rather just kept running), looking straight ahead. Finally, thankful that my transition was a glass-off.

Commit to your landing zone

In hindsight, some always question whether you could have waited a bit longer, gone higher, or flown further.

But in the end, when you decide to exit - make sure you commit to it.
Commit to everything you have.
Make it the best lineup to that final position.

Try to enjoy the view and the journey.
But never celebrate too early before returning to Earth!


Advice for new founders or board advisors

Meet an international cohort of about 400, while taking 9 courses in the online "mini-MBA" designed to put theory into practice. It is also perfect if you plan to be a product manager or build a startup.

For my 18-month journey from launch to exit, those classes and the online community during the pandemic were my sherpa and North Star. Outside of traveling to silicon valley, you can't beat the immersive experience.

For my alumni referral, please use my name, "Jacky Cheong" - part of the Voyager Cohort.

If you get selected, within the Workspace app, you can send me a message! I will help you start on your journey, just as the sherpas before me.

Learning to smile again

With the altitude and favorable winds, you can take a few pictures or take a few turns to get a full 360 view. It was scary at first to steer. You actually feel better if you feel brave leaning into the turn with a smile.

At some point, you have to accept the facts:

Gravity has you by the balls.
Air doesn't care.
Bank accounts weigh nothing.
So just sit back and relax.

As the saying goes...
"Life is short, and so are my legs."
(A few NIH studies about the benefits of being short)

ABC: Awaken, Begin again, and Continue the next climb.

I woke up the next morning before sunset, to start again.
Everyone was still asleep.
My phone's flashlight guided my way up the trail.

Make Hast.
Waiting for the first light to set out is a mistake.
You must be up there before the Sun's first rays peek over the ridgeline.

The sense of discovery and time scarcity spurs me forward.
I love finding a new mountain and capturing blue hour.
When you can rise before the rest, the mountain is all yours.

Next Episode (Part 3):
  • Reunion with my friend Cristina from Roma
  • Meeting the largest racket collector in Europe
  • Surviving a bad back on the floor at an Airbnb
  • Dealing with Nitto and their 700 Euro corporate seats
  • A meeting with tennis travel vlogger, Tsitsipas
  • My overall impressions of the ATP Finals for 2023